


The 12 Days of Wincestmas

by storyspinner70



Category: Supernatural
Genre: Alternate Universe - Canon Divergence, M/M
Language: English
Status: Completed
Published: 2018-01-09
Updated: 2018-01-09
Packaged: 2019-03-02 16:29:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 12
Words: 7,755
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13322079
Author URL: https://archiveofourown.org/users/storyspinner70/pseuds/storyspinner70
Summary: WHAT?12 days of anon love full of wincesty goodness, secret santa style!Anything goes- head canons, ficlets, edits, art, playlists, whatever!You just have to have anon enabled on asks/submit to receive your love!You’ll be expected to send at least one -thing- per day, but the more the merrier!





	1. Day One

**Author's Note:**

  * For [Sang_argente](https://archiveofourown.org/users/Sang_argente/gifts).



**_First Day of Wincestmas_ **

Momma always said there’d be a great love in his future.

Dean didn’t remember much from when he was a toddler, but he remembered when his mom read his tarot cards. He was three and could barely see over the table even with a stack of phone books underneath him. He thought they were going to play fish, but his mom said it wasn’t a game.

It took his mother two tries to get him to draw the cards, but he did it just to stop her mouth from turning down on the corners. It seemed important. He could tell from the look on her face – something he couldn’t interpret. Something he didn’t like. She didn’t say much afterwards, just looked at his cards in silence, her mouth tight in a way it never was.

She lifted him down from the table and told him to go play. Dean was happy to. Mom knew he hated to be inside on warm sunny days.

The next day, a woman with skin like chocolate and a loud voice came to visit. She held Dean’s hands, looking at them with the same intensity Dean used to plan his favorite army men’s next attack. She stared at him for a long time, then ran her fingers through his hair.

Dean could still feel the heavy weight of her palm curved over his scalp and the way she beckoned his mother over, her voice sharp and unsettling. For some reason, she stretched her other hand over his mother’s stomach, and Dean could hear whispering.

It didn’t sound like words Dean knew. It seemed like something Dean could feel more than hear, like little brushes of warm breath against his skin. He started to hum softly, a song he didn’t know. The whispering slowed down but didn’t stop. It never stopped again.

Mother always said there’d be a great love in his future. She had no idea it was a love that would bring the world to the very brink of destruction – then save it. She didn’t know the bond forged that night was one that would withstand everything literal heaven and hell threw at it. She didn’t know.

But everyone knows that the hardest steel is tempered by fire, and the strongest bond is no different.

Momma always said. She had no idea how right she was.


	2. Second Day of Wincestmas

**_Second Day of Wincestmas_ **

 

“My god I wish we were back in the bunker.”

“You and me both, Sammy.” Dean glanced up from where he was wrestling with his boots at the door of the unfortunate motel room they’d ended up in. “What’s going on? You okay? Get your clothes off.”

“I’m trying to decide if it’s better to just stay like this.”

“You’re coated in vampire blood, Sammy, you can’t stay like that. You already called the first shower, now go on or I’m going to take it for myself.”

“Yeah, except it’s colder inside the room than it was outside, and frankly, at least the blood is an extra layer.”

“Gross,” Dean laughed, walking over to Sam and wrestling him out of his clothes. “It’s not the first time we’ve frozen our balls off and I highly doubt it will be the last. Look, I’ll get us some clothes while you start the shower. If we’re lucky it’ll at least be warm. We’ll shower together, dry off on those tissues they call towels and jump right into some warm sweats and watch some _Casa Erotica_ under the covers while we slowly die of hypothermia. What do you say?”

“No wonder all the ladies like you, you charmer you,” Sam replied dryly as he fiddled with the water.

“They can’t help themselves, you know that Sammy. It’s my burden to bear. But don’t worry,” Dean came up behind Sam, wrapping his arms around him. “You’ll always be my very best girl.”

“I will bite you, Dean. And not in that place you like so much, either.”

“But...”

“If you say one thing about my hair, Dean, I swear...”

“I wasn’t!” Dean interrupted loudly. “I mean, not now anyway.”

“Alright Dean, hop in, the water’s as warm as it’s going to get.”

“Oh, shit, that’s...Come on Sammy, hurry. Holy...”

“How far away is the b-bunker anyway?” Sam ground out through chattering teeth, his skin so cold he barely felt Dean scrubbing his hair and body.

“About eight hours. Too far for us right now. I’m so tired, Sammy.”

“I know you are. Me too,” Sam sounded so defeated.

“Okay you’re all clean. Get dried off the best you can while I finish up, then get dressed. Two pairs of socks, Sammy. They’re laid out on the bed.” Dean set to scrubbing his own body as Sammy did as he was told. “And keep your hair in that towel, you hear me, princess? Your giant brain will be a block of ice before morning if you don’t.” He could hear Sam grumble something in response, and assumed it was just his brother thanking him for being such a caring big brother as usual.

Sam had just climbed under the frigid covers when he heard the water stop and Dean cursing as he dried off with the small, threadbare towel. “We’re not hunting until spring, Sammy. I mean it!”

“Sure, Dean. I hear you.”

“I hope you don’t want any tonight, Sammy. I’d be too afraid something necessary would snap off in the cold.”

“Have you always been this dramatic?”

“You say dramatic, I say practical,” Dean laughed as he dove under the covers and wrapped himself around Sam in one smooth, practiced move.

“It’s actually not that cold under the covers as long as you cover your head up. And don’t move. And pretend you’re in the Bahamas.”

“I always liked Hawaii more. We need to go there. I’m sure there’s plenty of things that go bump in the night there. It’s our civic duty, Sammy.”

“You have to take a plane to get there.”

“There’s boats.”

“Ships, Dean.”

“Whatever. Hold me, Sammy.”

“Shut up, Dean.” 

“Disrespectful...When I can move again you’re gonna regret that.”

“Uh huh,” Sam sighed, his body relaxing as Dean’s warmth finally sank into his skin. He inched toward his brother, tucked into his normal spot, and let Dean’s warm breath flow across his cheek and chin. “Night Dean.”

“Night Sammy.”


	3. Third Day of Wincestmas

**_Third day of Wincestmas_ **

 

“Dean. Wake up, Dean.”

“What time is it?”

“I don’t know, it’s still dark.”

Dean rolled over, searching for the brother that was usually plastered to his side. “What’s up, Sammy?”

“Do you ever regret...us?”

“Which us, Sammy? Brothers? Hunting partners? Lovers?”

“Yes.”

Dean scrubbed his hands over his face and ran his fingers through his hair, heaving himself up in the bed. “What brought this on at...” Dean scrambled for his phone, “...four o’clock in the morning?”

“I just...couldn’t sleep.”

“Sammy.”

“I keep having dreams...”

“Dreams or visions?”

“Dreams, Dean. I haven’t had visions in awhile now, you know that.”

“Just checking, Sammy. What dreams?”

“Sometimes it’s Dad and sometimes it’s Bobby. They found out about us when they...when they died. They’re not happy about it.”

“Come here, Sammy.” Dean beckoned Sam closer. “Come on, get over here. Don’t make me drag your ass over here.”

Sam snorted, “Like you could.”

“Don’t think that just because you’re overgrown that I can’t still take you.”

“What if they hate us now, Dean?”

“Oh, baby. Look, you know how I feel about both of them.”

“Yeah.”

“But you also know how I feel about you.”

“Do I?” Sam asked, slanting Dean a look out of the corner of his eye, his lips twitching.

“I sure hope so because it’s too early for a full on chick flick moment. This is bad enough.”

“It’s not a mistake?”

“What is this really, Sammy? Do you not want to do this anymore? You gotta tell me, man, if that’s what this is.”

“No! Dean it’s not that. It’s just the dreams...”

Dean settled back in bed, dragging Sam down with him. “Do you remember the siren, Sam?”

“Of course,” Sam snickered. “It’s what got us back together.”

“Exactly. Remember what that dick of an angel told Adam?”

“About us being erotically co-dependent?”

“Yes. And remember how much junkless hated us?”

“He really did.”

“Yeah, because he couldn’t stand that we had a love that sure as hell shouldn’t exist but does anyway. That we have always been all wrapped up together so tight that not even angels can separate us. That God himself knows all about us and there wasn’t one damned thing junkless could do.”

“It could also have to do with the fact that you always called him junkless.”

“Whatever. It was true.”

Sam laughed a little. “Do you ever wish things were different?”

“Sometimes.” Dean could feel Sam stiffen beside him. “I wish we weren’t hunters sometimes,” he continued, “that the things in the dark weren’t real. That prisons were all we needed to take care of the bad guys.”

“What do you think our lives would be like?”

“I don’t know. I think I’d be a cop, maybe. Or a mechanic. You’d be a lawyer, of course. Or maybe not. You only got into law to begin with in case you had to bail me or Dad out, right? Hmm. Maybe you’d be a librarian. God knows you love to get your geek on.”

“Hmm,” Sam hummed, voice getting thick and heavy with sleep. “Maybe. You think we’d be together?”

“Did us being Smith and Wesson not teach you anything?”

“Oh, true. Sometimes I forget some parts of our life are actually real.” Sam paused, inching closer to Dean. “So you don’t think we’re fucked up?”

“Oh, I think we’re massively fucked up, Sammy,” Dean replied fondly. “Definitely fucked up.” Dean leaned down and pressed sloppy kisses over Sam’s face until he grunted in displeasure and tried to push Dean away. “But I wouldn’t change a thing, Sammy. Not about me, and not about you and not about us.”

“So you’re saying...” Sam paused dramatically, “...that we were born this way?”

"What?" Sam could feel Dean start to tense up. “I swear to god, Sam, if I get in Baby tomorrow and it’s on one of those trash pop stations you love so much, I’ll never let you drive again!”

“You knew what I was talking about though,” Sam responded smugly.

“I mean it Sammy!”

“Sure you do,” Sam slurred, sleep hitting him hard. “Sure...”

Five minutes later, Dean headed outside in just his underwear and boots. Sam lay still until he heard the door open and the sound of Baby starting up. Dean’s “Son of a bitch!” was just loud enough to carry into the room.

If Sam fell asleep giggling, it was no one’s business but his own.


	4. Fourth Day of Wincestmas

_**Fourth Day of Wincestmas** _

  
_Baby Gets a Bath (1/2)_

 

“Need any help?’

Dean stopped for a moment then looked at Sam. “Christo.”

“Funny,” Sam snarked back. “You’ve been out here for awhile, and I wanted to see if you needed any help, is all. Forget I offered.”

“Oh, no, Sammy, it’s out there, you have to help now.”

Sam just snorted. “Sure you want me touching Baby?”

“Don’t be jealous Sammy. You know I love you almost as much.”

Sam just laughed.

“I’ve already cleaned her, and there’s no way I’d let you wax her after what happened last time, so...”

“I missed one tiny spot, Dean, it was hardly that traumatic.”

“The entire passenger side, Sammy. That is not ‘one tiny spot’. How about you polish her wheels?”

“It’s not my fault you kept distracting me,” Sam said as he brushed by Dean to get to the tire and rim products. Glancing out of the side of his eye, he noticed Dean was watching appreciatively as he bent over. Straightening, he made his way to Baby, dropping to the ground by one of the wheels.

He and Dean kept trading glances as they worked, Dean arching his brow and licking his lips while Sam answered with dimples and hiding behind his bangs. Soon enough, Sam was done with the tires and rims and was looking for another reason to stay outside.

“Maybe clean the inside,” Dean suggested.

“You got it,” Sam replied. An idea struck, and Sam opened both doors to the back of the car. Starting with the leather protectant, Sam rubbed the sides of the back seat he could reach comfortably, his hips swaying as he wiped. He moved onto the front seats, then the floor mats, and dragged the wet/dry vac out and started carefully cleaning the carpet up front when he was done.

Dean stopped what he was doing to grab a beer, but his eyes were more on Sam than his drink. When Sam was done, Dean was just finishing his beer.

“Uh oh, I think I missed a spot again,” Sam said.

“Again? Come on Sammy, be good to Baby.”

Sam made a big show of slipping off his boots and climbing on all fours into the back seat. “Just couldn’t reach the middle here, is all. Don’t worry, Dean. I’ll get it done.” Sam looked back. “I forgot my rag. You think you could get it for me?”

“What are you doing, Sam?”

“I just wanted to help, big brother.” Sam flipped over and slid forward so he was on his back, legs splayed wide and out the door. “Didn’t I do a good job?”

Dean narrowed his eyes at Sam, then walked over to stand between Sam’s legs. He leaned into the car and planted one hand against the back of Baby’s seat, his thigh rubbing up against Sam’s. “Hmmm, other than the spot you missed, it looks good, Sammy.” Dean paused and leaned down, his breath warm across Sam’s sweaty throat. “Looks _really_ good, Sammy.”

Sam looked up at him steadily.

“We’re outside, Sammy.”

Sam didn’t say a word.

“You just cleaned the seat,” Dean whined, staring back at Sam. “Goddammit,” he whispered. “Pants off, Sammy, and get back on those knees. That was one sight I definitely want to see again.”


	5. Fifth Day of Wincestmas

_**Fifth Day of Wincestmas** _

 

_Baby Gets a Bath (2/2)_

 

“Ah, fuck, Dean I’m good, just...”

“Just what, Sweetheart?”

“You’re driving me crazy. Prep is good. Prep is great. Prep is done. Fuck me.”

“I don’t think so, Sammy. I think I’m in the mood for something else right now.”

“What? No...”

“Oh, yes,” Dean interrupted. He sat back for a second, hanging in the door way, his brother on elbows and knees in the back seat. “Raise up and move closer to the door.”

“Dean?”

“Go on, one foot on the floor, lean on the door, arms up.” Sam hesitated but finally started to move.

“De...”

“Shhh, sweetheart.” Dean turned his back and lay down, sliding until his face was underneath where Sam was hovering uncertainly over the seat. “Comfy?” He asked.

“Come on, Dean,” Sam’s voice was strained, deeper than normal, cracked in two with impatience and desire.

Dean turned his head and latched his teeth into Sam’s inner thigh, a sharp but shallow bite meant more to prod Sam than cause any real pain. Sam jerked his knee into the front seat and he stiffened, trying to rise from his position against the door. If anyone knew Sam’s reflexes though, it was Dean, who simply set his elbows to the seats on either side of him and grabbed Sam’s ass in both hands.

Sam drew in a sharp breath, but stilled.

Dean sank his hands into Sam’s ass, dipping his thumbs into Sam’s crack and separating them. Sam shivered when Dean blew gently over Sam’s taint and hole. 

“Dean, I swear to god...”

“Easy, baby.”

“You talking to me or the car?”

Dean swept the flat of his tongue over Sam’s taint in reply. He leaned up, sucking the smooth skin between Sam’s legs, scraping his bottom teeth over the seam, following it to Sam’s hole. He switched between pointing his tongue and tracing Sam’s loosened hole, dipping inside, and laving every spot of skin he could reach with broad strokes.

It didn’t take long until Sam was groaning above him, holding his breath one minute and cussing the next.

“Dean, touch me, please.”

“I don’t think I can reach. You’re gonna have to take care of yourself.”

Sam immediately reached for his cock, stroking and twisting in as close a rhythm to the erratic pleasure of Dean’s mouth as he could get. “Oh, fuck. Dean. So close.” Sam muttered, his back curling and his breath coming faster and faster.

“Come on, sweetheart,” Dean hummed against Sam’s skin. “Come for me.”

Soon enough, Sam did, thighs shaking on either side of Dean’s head, his mouth wide and eyes slammed shut.

“That’s it, Sammy. That’s it, sweetheart.”

They shifted, years of practice fitting into tight spaces making it smooth and easy.

“Need help with that?” Sam asked, lifting his head from the seat back to indicate the hard line of Dean’s cock in his jeans.

“Nah. This was for you, Sammy. I’ll take care of it in the shower.”

“Mmm a shower sounds nice.”

“Yes it does,” Dean said. “I’ll be done by the time you’re done out here. Don’t worry. I won’t use all the hot water.”

“Out here? What?”

“You came all over my door, and sweated all over my seat Sam. You can’t just defile Baby and not clean it up.”

“All for me, huh?” Sam said sourly.

“All for you, baby.” Dean leaned over and kissed Sam soundly. “And don’t forget to put the stuff up.”

Sam was still sputtering when Dean slid across the seat and out the door. “Oh,” he said, popping his head back in. “or that spot you missed earlier.”


	6. Sixth Day of Wincestmas

**_Sixth Day of Wincestmas_ **

__

 

“God, Sammy. I’m so tired,” Dean dropped their weapons in the trunk and thunked it closed. “Fucking angels.”

Sam handed Dean a beer. “Me too,” he started. His stomach growled, a long, deep, unhappy sound. “And I’m hungry.”

Dean just snorted. “Come on Sasquatch. Finish up your beer and we’ll go. Fast food and head to the bunker or diner food and a cheap motel?”

“What kind of girl do you think I am? Diner and the bunker. Cheapskate.”

Dean groaned. “Fine, but if I get tired, we’re pulling over somewhere.”

“I _could_ always drive you know.”

“After what you did to her while I was gone? No way, Sammy.”

“Hey," Sam said, "did I ever tell you I was glad you were back?”

“You might have mentioned it once or twenty times.”

Sam just smiled at Dean, hell still too close for his comfort.

“The solid week of non-stop sex might have clued me in, too.” Dean laughed then stood just looking at Sam for a moment - smile soft and sad around the edges. “Come on Sammy. We’ve miles to go before we sleep.”

“Did you just...”

“I’m just full of surprises, Sammy boy. You should know that by now.”

"Yeah. I really should."


	7. Seventh Day of Wincestmas

_**Seventh Day of Wincestmas** _

_**** _

 

“Look at those stars.”

“I almost lost you tonight. Fuck those stars.”

“Sammy..”

“Don’t, Dean. You can’t keep...”

“I can, and I will.”

“Fuck you, Dean.”

“Alright that’s enough. I got a little banged up, a bad shoulder. It’s been a lot worse. You’re not exactly undamaged yourself, so I don’t know why you’re losing it now.”

“It’s not about your injuries, Dean. It’s about the fact you deliberately put yourself in front of two angels that _we cannot kill_ just to keep them away from me.”

“It’s my job, Sammy. And I won’t apologize to you or anyone else for doing it.”

“Do you know how I feel when you do things like that Dean? Do you even care?”

“Of course I care, Sammy. Look at me.”

Sam heaved a sigh but turned to look at his brother.

“How many times have we had this discussion, Sammy?” Dean grabbed Sam when he would have turned away. “Come on Sam. I get it, okay? I understand you don’t want me to put myself out there like that for you. And I know. I’ve heard you. Every time you’ve told me you couldn’t live without me, I have heard you,” Dean stressed.

“Then why don’t you _listen_?”

Dean sighed. “Oh baby. I’ve been protecting you for almost 25 years now. I know it drives you up the wall. I know you want to kill me most of the time. But you will always be infinitely more precious than I am.”

“Goddammit, Dean.”

“Enough, Sam. Kiss me, sweetheart.”

Sam did, fingers tight in Dean’s hair, mouth hard, teeth sharp. Later, looking up at Dean from the backseat of Baby, Sam would catalog every bruise, cut and scratch that marred his brother’s beautiful body.

“You’re everything to me Dean. So all this you’re doing to try to save me? It’s a waste.”

Dean opened his mouth to argue, but Sam went on.

“You get yourself killed? I’m going to follow. No! Close that mouth, Dean, unless you’re planning on sucking my dick again, because this is how it is and how it’s going to be. You die, I die. And that’s the rest of the story.”

Sam and Dean stared at each other, at a stalemate like always.

“What you gonna do Dean? You can’t rock, paper, scissors your way out of this one.”

“Come on, Sammy. Let’s find a motel. I’m tired, and my shoulder is killing me.”

Stretching out after the cramped backseat, Sam slammed the door and stopped for a moment, hands on the roof of the Impala. “You were right. The stars tonight are beautiful.”

“Let’s go, Sammy. I’ll show you what beautiful is.”

 


	8. Eighth Day of Wincestmas

_**Eighth Day of Wincestmas** _

_**** _

 

It started like most things – an extension of their love for and their anger at each other. Trading punches became trading kisses – wet, hard jabs that might as well have been slaps. Most of the time it started with a look, a touch, a wicked smile. Sometimes it started and ended with screaming. That’s not really all that important.

What is important is the fact it started at all.

They both pulled back – one then the other – but it was like carving thunder apart from lightning. They might separate, but they would always exist in the same place at the same time. And when they finally found their way back to each other, it was enough to set the world on fire.

Oh, at first it was only when they fought – better and safer than picking up someone that could easily be a demon in disguise, just another outlet that didn’t involve fists (not at first, anyway), a normal reaction to living a life so tied up with each other that everyone else all looked the same anyway.

There were a lot of ready lies to make it wholly and fully…reasonable.

Then Dean pulled on a priest collar and Sam barely made it through the dead man’s wake and back to their shitty motel before he had Dean pinned to the wall, door still open, rutting against his brother until Dean came in his cheap black pants. Moments later, he found himself smashed face down into the filthy motel bedspread, his brother’s hand tight around the back of Sam’s neck and firm on the small of his back, giving him nothing else to rut against for relief.

He’d dragged his brother off to “change” almost immediately after they returned from 1861, Dean fully dressed, his leather duster flared around them like a shroud on Bobby’s lumpy, worn guest bed.

It was a dark alley the night Dean came back from 1944 with an attitude, a shoulder holster and a custom fitted suit.

The day Dean found out Sam was wearing a pair of panties, he ended up fucking Sam in the stall of a halfway clean diner, Dean’s hand clamped to Sam’s mouth, his teeth tight against Sam's shoulder.

Yeah, it started like most things do with them – a reason not to talk, a bid to work things out without actually working them out. But it continued like everything with them, as well – an electric storm that served only to tighten an already breakable bond.

Because you can have lightning without rain, but never without thunder.

 


	9. Ninth Day of Wincestmas

_**Ninth Day of Wincestmas** _

 

_**** _

 

_Changing Channels – After Dark_

What about the channels we didn’t see? For the last four days of Wincestmas, I’ll tell you stories from these shows – and you’ll get more of the image every day. No nudity, but still NSFW.

****

Sam zapped out of the sugary sitcom he and Dean had been stuck in, and looked around quickly to see what situation they’d found themselves in now. He didn’t see his brother anywhere. It looked he was in an apartment. Nice furnishings. Everything looked normal except the fact the cabinet under the kitchen sink was standing open. “Dean?” Sam continued through the apartment. “Dean? Where are you? Hello?”

There was a knock at the door. Sam took a moment to check the peephole. “Dean, thank god.” Sam pulled open the door. His brother was standing there, a toolbox at his feet. “Dean?”

“What’s up, Sammy. Did you figure out what show we’re in now?”

“Are you...” Sam stopped for a second. “Are you a plumber?”

Dean was dressed in skin tight jeans, work boots and a tattered tank top. “I think I am.” Dean sifted through his toolbox as he entered the apartment. “Looks like plumbing stuff to me. Do you have...”

“Dean?” Sam prodded Dean who seemed to be frozen in the middle of the living room, his eyes wide and his mouth open. “Dean, what is it?”

“What are you wearing, Sammy?” Dean’s voice crept out of his throat, dark in a way it only was when he was angry or horny, and jagged like he’d been screaming for hours.

“What?” Sam looked down at himself. “Oh, god. What the hell?” Sam jerked his shirt closed and started cussing the Trickster as he looked around the apartment for more clothes. “I can’t...oh, that asshole...You just wait until I get hold of you, you...”

“Sam.” Dean spoke quietly. “Come here.”

“Dean...”

“Let me see, Sam.”

Sam stopped in front of Dean, and dropped his arms. Dean brushed his hands over Sam’s naked thighs, sliding his fingers up and under his open shirt to the pink satiny panties underneath.

“Dean...” Sam tried again.

“Shhh. Busy, Sammy.”

“Dean, please.”

“Please what, Sammy?”

“Touch me, Dean.”

“I am, Sammy.” It was true, technically. Dean was rubbing his fingers lightly over Sam’s growing erection, watching as it lengthened and pushed out of the panties. “What pretty pink panties, Sammy. You know how I feel about you in panties. And your matching bra, too.” Dean leaned forward, pulling the cup of Sam’s bra down with his teeth, anchoring it with his chin so he could suck Sam’s nipple into his mouth.

“Dean, come on.”

“So impatient, Sammy. Fine, let me take care of this.” Dean waggled his brows and dropped to his knees. He had Sam’s cock halfway down his throat, when he stopped suddenly and pulled off. “I’ve seen this show,” he said, swallowing his spit and Sam’s precum.

“Everyone that’s ever seen porn more than twice has seen this show, Dean. Get your mouth back...”

“No, Sammy, I’ve seen this exact show. Casa Erotica, last week. The woman had the same clothes on. She...oh, you’re not gonna like this, Sammy.”

“Oh, god. What?”

“Never mind. It’ll be fine, but we have to go to the kitchen. I need to fix your sink.”

“What? Dean, no, what am I not gonna like?” Sam just stared after his brother. “Dean?”

“Get a move on, Sammy. I need to lay some pipe!”

“You’re not funny, Dean. Tell me what’s going on!”

Dean snapped on a thin rubber glove and reached for a bottle of lube conveniently placed on the counter. “You know we have to play along, Sammy.” Dean grinned, wide and toothy.

Sam just groaned, looking suspiciously at Dean’s gloved hand. “Where you want me?”

Dean dropped to the floor, head under the sink, his pants pulled to right under his balls, wide grin still on his face. “Ride me, sweetheart.”

Sam lowered himself to Dean’s lap and slid Dean’s underwear down and his own panties to the side. “Cowboy it is.”

 


	10. Tenth Day of Wincestmas

_**Tenth Day of Wincestmas** _

_**** _

 

Sam had just come all over Dean’s chest, his brother still buried inside him when Dean mentioned the next part of the show.

“You want to _what_? Not a chance in...”

There was a moment of blackness, and a swooping to his stomach that Sam was frighteningly used to by now. Sam steadied himself quickly, looking for immediate dangers first, then checking to see what he had on.

“Damn you, Trickster, what is this!” Sam’s long slim legs were encased in fishnets held up by garters that tucked under his – frilly black skirt. “I swear to god!”

“Sammy.”

Dean. Sam whirled around, ready to bitch about his clothes, but didn’t get the chance.

“I think you need to see this,” Dean said, his voice low and rough as he studied Sam’s latest outfit.

Sam followed him into the room Dean indicated, catching his breath when he processed what was in the room.

Dean was standing at a high table, his broad back swathed in a suit that fit him far better than anything Sam had seen on him before. His fingers were trailing across the items on that table – crops and canes and floggers and restraints. The rest of the room was filled with a large bed and item after item Sam was surprised he recognized.

“Dean.”

“We need to talk about this, Sammy.”

“Dean, look at me.”

“I don’t think I can right now, sweetheart.”

Sam stood behind Dean, running his fingers over the thick black cuffs on the table. Dean’s hand covered his own, then slid up his arm to his shoulder. Dean stepped left and back, reversing their positions. He hooked both hands under Sam’s arms, and pressed him forward until his hardening cock was trapped painfully between the wide leg of the table and Sam and Dean’s combined weight.

“What do you have to say to me, sweetheart?”

“Kansas,” Sam whispered.

“I didn’t hear you. Speak clearly.”

“My...my safeword is Kansas.”

“Good boy.” Dean reached around Sam to pick up one of the cuffs, buckling the wide leather to Sam’s wrist. “Know what good boys get, sweetheart?”

“What?” Sam whispered, his voice little more than a breath.

“Good boys get to choose. Anything you want, sweetheart.”

Sam hesitated for a moment. “Go. Now. Or I’ll choose. And I’ll make sure it’s not something you enjoy.”

Sam quickly reached for a leather wrapped paddle and made his way to a sumptuously padded bench. He stood quietly, head down, as Dean walked to the bench and made himself comfortable.

“Good choice, pretty. On my lap.”

Sam started to lie across Dean’s legs, but Dean stopped him. “No, pretty, straddle me.” Sam did, his back bowed and his head down.

“Trickster sure has a thing for you in girly things, doesn’t he?”

Sam didn’t answer, but he could feel his face on fire with embarrassment.

“How come I never noticed you blush clear down your chest, sweetheart?” Dean slipped his hands up the outside of Sam’s thighs, hesitating when he didn’t feel panties like he expected. He then ran the flat of his palm over Sam’s ass to verify there were none. “Oh, pretty, this is going to be such a good night.” Dean paused for a moment, kneading the cheeks of Sam’s ass with both hands. “Ass up, sweetheart.”

Sam hurried to comply, rearranging himself over Dean’s lap.

“I need to know, Sam, that you’re okay with this.” Dean spread his hand over Sam’s back. “I need to know you want this, because this is a line we’ve never crossed, and I’ll stomp all over that line if it’s what you really want. But we’re not doing this if you have the tiniest bit of doubt. Understand me, Sammy?”

Sam nodded quickly.

“I need to hear you say it, Sammy. And I need to believe it.”

It was as if Sam had forgotten how to speak for a moment, his voice creaking out of his throat like it had been months instead of moments. “I want this, Dean. I do.”

“And you’re not doing it just because of the Trickster? Because, I’m telling you, Sammy, I will burn this world to ashes if you don’t want it.”

Sam leaned up and twisted, one hand on the edge of the bench, and one on the back of Dean’s head. He stared at Dean for a moment, willing him to get what Sam didn’t want to say.

Dean must have been satisfied with what he saw in Sam’s ever changing eyes, because he pushed him back down and said, “Alright, sweetheart, let’s get started.”


	11. Eleventh Day of Wincestmas

_**Eleventh Day of Wincestmas** _

 

_**** _

 

Sam’s ass was on fire. He cried out in pain and pleasure every time Dean fucked into him, scraping against his battered cheeks with the stiff fabric of his suit pants.

“Come for me, Sammy.”

Before he could, there was the sickening swirl and darkness. Sam came to screaming.

“Goddamn you, Trickster!” Shocked gasps met his yelling, and Sam turned, taking in his newest surroundings. A fucking church. With people in it. Sam quickly checked his clothes, relieved to find himself in a nice suit. Scanning quickly, he searched for Dean, but didn’t see him anywhere.

As he searched, he found the restrooms and stepped in. His hair was pushed back on top and curling by his ears. He has long widening sideburns and his suit was actually a tux, bow tie, cummerbund and all. He looked sophisticated and cosmopolitan in a way he’d never imagined for himself – even when he was Stanford.

His story came to him in that moment. He was getting married.

No, he was supposed to get married but didn’t. Flashes came to him then solidified into one horrible picture – he didn’t get married because the bride had caught him buried balls deep in one of the groomsmen an hour before the service. The hurt on her face might not have been real, but it sure felt it.

Leaving the bathroom, he made his way back through the nave of the church, avoiding the still censuring eyes of the worshipers seated there. He decided to hide out on the confessional until Dean showed up.

“How may I help you, child?”

Sam’s head whipped to the latice that separated him from the priest offering forgiveness. “Dean?”

“How long has it been since your last confession, Sammy?”

“Dean...”

“How long?”

“It’s been 27 years, _father_.”

“And what’s on your mind, _my son_?”

“I...” Sam struggled to remember things he’d seen on TV and during their investigations that would help him with what he was supposed to say. “Forgive me, father for I have sinned.”

“Tell me how.”

“I...I cheated on my fiancee.”

“Really? When?”

“Today? I think.”

“With who?”

“A groomsman.”

“I see. Adultery and sodomy. I take it she was a little unhappy?”

“I assume so.”

“Five _Hail Marys_ and one _Glory Be_.”

“Al...Alright. Thank you, father.”

“What about the rest of it, Sammy?”

There was silence for a moment in the sweltering heat of the confessional. Sam studied the outline of Dean’s face barely discernible through the lattice work. The strong jaw and thick neck. His short hair.

“I let my brother fuck me whenever he wants,” Sam whispered.

“And why is that, Sammy?”

“Because I want it. Because I’ve always wanted it. Because no matter what happens in this world or the next, he only sees me. Because he would tear it all down with his bare hands if I asked him to.”

“Anything else?” Dean’s voice sounded rough and strangled.

“I like wearing women’s lingerie.”

“Do you?”

“It was just panties at first, for y-for my brother, because I knew it would drive him crazy. But lately, very recently, in fact, I’ve found I like stockings, too, and garters, I think they are. There – there was a ruffly skirt I kind of liked, too, but that may have been because my brother beat my ass with a paddle through it before he folded it up and stuck the handle...”

“Sammy.” Dean’s voice was sharp and darker than Sam had ever heard it. “Turn around and stand as far against the wall as you can.”

Sam did, only turning when he heard a sharp, crackling thump. Dean broke the lattice separating him from Sam, making sure it was all gone before looking at Sam. “Clothes off, then turn back around, ass to the hole.”

“Dean...”

“Now, Sam. I won’t say it again.”

“Dean this is a church.”

“Sam. None of this is real. Do what I said.”

Sam did as he was told, his legs shaking at the pure gall of doing this in a church.

“Hold your ass open for me, Sam. There we go.”

Sam braced himself, expecting the blunt, sharp intrusion of Dean’s fingers, but startled when he felt the warm wetness of Dean’s tongue instead.

“Did you let that man fuck you, Sam? Is that what she walked in on? You getting your little ass fucked? Did you moan and cry out with him like you do me?” When it took Sam a moment to answer, Dean bit down on Sam’s ass, shocking him.

“No! No, Dean. I...I fucked him.”

“I see.”

“Wouldn’t...wouldn’t let someone else fuck me, Dean, not even in a dream world.”

Dean pulled his face from Sam’s crack long enough to murmur his approval. “Good boy, sweetheart. Such a good boy.”

“Dean...”

“You didn’t get to come before this last trip, did you?” Dean sunk two fingers into Sam, zeroing in on his prostate and knocking against it. “Come on, Sam. Let go.”

“Dean, it’s a church, I can’t...”

“Yes you can. Now, Sam.”

Sam came then, dropping to his knees in a bid to stay quiet, to keep his and his brother’s massive sin to themselves.

Dean groaned quietly, and Sam felt the warm slide of his brother’s cum down his back.

“You are forgiven, my son.” Dean laughed. “Get dressed, Sam. Here, use my shirt to clean up.” Dean struggled out of the top he’d had on under his robes.

“We’re going to hell.”

“We’ve already been, Sammy. Ain’t nothing to be afraid of now.”


	12. Last Day of Wincestmas

_**Twelfth Day of Wincestmas** _

 

_**** _

 

Sam hurtled through space and time and whatever else again. All black nothing and churning guts. When he came to, he simply lay still for a moment. Glancing down, he snorted. More panties, of course. From what he could see, these had ruffles all over the ass and matching stockings in a pretty pale pink. Dean was gonna love this.

Speaking of Dean, Sam lifted up a bit to see where he was and if he could see his brother. There was a weird haziness to the room, but Dean was nowhere to be seen. Suddenly, there was a loud thud against the door.

Sam only had enough time to turn before a fireman burst through his door, ax quickly shredding through the cheap wood. The fireman searched quickly until he found Sam on the floor, then came to stand over him.

“Dean?”

The fireman said nothing, just stared, taking in Sam’s naked chest and long silk clad legs.

“Dean?”

The fireman crouched down, pulling Sam to his feet then quickly hoisting him over his shoulder, one hand around his knees, the other buried in the ruffles on Sam’s ass. Sam could feel his fingers digging through his panties, finding his crack and anchoring there.

He could feel his cock start to harden, the silk of his panties sliding against his skin in the places that weren’t being rubbed raw by the fireman’s heavy, rough coat. The fireman stopped briefly by the couch and grabbed the blanket there to throw over Sam’s draped body.

Sam thought at first he was just being solicitous, covering Sam’s mostly naked body, but once they cleared the apartment, it became clear it was mostly _because the building was actually on fire_. Fucking Trickster. Sam swore for what must have been the thousandth time that the Trickster was going to die this time for certain. He’d hunt him down and stake him personally, face to lying, scheming face.

Sam was pretty sure the Trickster was having a grand old time torturing them, but he hadn’t actually tried to hurt them – bar the Nutcracker and Sam’s sudden case of herpes in that commercial. If something had gone wrong, Sam could have easily died of smoke inhalation while he was looking for Dean. And what if Dean had gone to another floor instead of the one Sam was on? Sam was getting more mad with every step they took.

The fireman Sam was pretty sure was Dean obviously picked up on Sam’s ire by the stiffening of Sam’s body as he hung over the man’s shoulder. The man dug his fingers into Sam’s ass, squeezing the cheek he had hold of hard enough to hurt.

“Sorry,” Sam muttered, aware the man would never hear him. Taking a breath under the suddenly oppressive weight of the blanket, Sam forced himself to relax. They soldiered on, the air getting hotter and hotter. Sam grabbed a handful of the cover and pulled it tight to his face, the smoke making it hard to breath.

Sam could hear the sound of the fireman’s breathing equipment and the frighteningly close crackling of the fire. His heart was pounding and his own breath was loud in his ears. He was covered in sweat, was light headed from hanging so long upside down and was entirely too aware of the fat gloved fingers burrowed into his ass.

Suddenly, the air lightened, and Sam could hear muffled shouting. The smoke cleared and Sam could see grass beneath the fireman’s heavy boots. Thank god, they were safe. Still killing the Trickster though. Now more than ever.

The fireman walked longer than Sam expected, and he was starting to worry. Maybe Dean was just trying to get them away from people. That was it. But there was a niggling at the back of his mind that kept repeating _you don’t know that’s Dean_.

The fireman stopped abruptly, dropping Sam and turning off his steadily beeping breathing equipment almost simultaneously. Sam staggered a bit, the sudden change in orientation and the fact he was still covered making him clumsy. He bumped into something hard, and after a moment determined it was some kind of wall and probably safe to lean against. He slumped there for a moment before he started pulling the blanket off of him.

“Dean...”

Before he could finish, the still suited fireman turned him around and pressed him to the wall, kicking at his ankles until Sam spread his legs. The fireman hadn’t removed any of his equipment but the breathing tanks and Sam was beginning to get mad. If the man was Dean, he was going to pay for startling Sam like this, and if he wasn’t, well, Sam would take care of that, too.

He pushed away from the wall, but found his cheek pressed to the rough wall and held into place with a smoky leather glove. The man’s other hand slid down inside his panties and Sam bucked against him, but he accomplished nothing but scraping his face on the brick. Sam could feel the thick leather of the fireman’s gloves stroking up and down his crack, pausing over his hole.

Dean or not, there was no way Sam was going to let someone finger fuck him dry with rough, thick gloves. The fireman had yet to make a sound. Sam kept struggling.

The fireman palmed Sam’s hip and jerked Sam’s ass toward him. He moved his hand and was jerking Sam off roughly before Sam figured out exactly what was going on.

“No! Dean, if that’s you, I’m going to...I’m going to kill you.” Sam couldn’t help but moan as the fireman’s rough glove scraped over the head of his cock. “I’m not...You can’t...” In moments, Sam was coming. The fireman stepped back, leaving Sam leaning against the wall, his pink panties askew.

Sam could hear him removing his equipment, and when he could, whirled around just in time to see Dean pulling the helmet off his head. His face was flushed, a bright red over his cheeks and chin – probably a combination of the super heavy equipment and the sky high temperatures in the fire. His body was soaked with sweat and his hair was plastered to his head.

“Dean,” Sam groaned, stepping toward his brother. Dean raised his arms as if to hug Sam, so when Sam drew back and punched him as hard as he could, it caught him by surprised.

“What the fuck, Sammy.”

“I wasn’t even sure it was you, you jerk!”

“Who the hell else would it be?’

“I don’t know, but you never said a goddamn thing! Why do you think I was struggling at the end?”

Dean crowded Sam against the wall. “Come on, Sammy, you might have been mad but you sure as hell didn’t let it stop your dick from getting hard, did you?” Dean started to grind against Sam’s hip. “Tell me, Sammy. Was it the panties or the stranger that got you so hot?”

“It was the _fire_ , Dean. We could have died! We...” Sam’s voice faltered when Dean slipped his hand back down Sam’s panties.

“Anything you say, Sammy. Anything you say.”

**

Yay, the last day! But also, boo the last day! I hope you enjoyed at least some of these days as much as I enjoyed creating them. I always worry I’m going to be a big disappointment. Hopefully, there were at least some days you liked. :D

I find myself hating to end this, actually. Lol I want to put Sam and Dean through even more Channels – like True Blood or Penny Dreadful or even Murder She Wrote or Monk or Roseanne. Lmao I might continue it on my own, who knows.

Thank you so much for putting up with me for 12 days! I had a lot of fun. :D


End file.
